1. Field of the Invention
The present invention relates to (3R)-1-menthyl 3-hydroxybutyrate and production method thereof and a sensate composition comprising the same. In addition, the invention relates to a flavor or fragrance composition, food or drink, fragrance or cosmetic, daily necessities and household goods, oral composition or pharmaceutical, which comprises the (3R)-1-menthyl 3-hydroxybutyrate or sensate composition.
2. Description of the Related Art
Up to now, cooling agents which exert a refreshing sense (refresh-feeling) or cool sense (cool-feeling), namely cooling effect, on human skin, oral cavity, nose and throat are used in dentifrices, sweets (e.g., chewing gum, candy and the like), tobacco, poultice, cosmetics and the like. As a flavoring substance which provides such a refresh-feeling or cool-feeling, 1-menthol (1-menthol) is now broadly used but its cooling effect has a weak point of lacking in persistency.
In addition to 1-menthol, a large number of compounds have been proposed and also used as the compound having cooling effect. In exemplifying the so far proposed compounds having cool-feeling effect other than 1-menthol, for example, 3-substituted-p-menthane (e.g., see JP-A-47-16647), N-substituted-p-menthane-3-carboxamide (e.g., see JP-A-47-16648), 1-menthyl glucoside (e.g., see JP-A-48-33069), 3-(1-menthoxy)propane-1,2-diol (e.g., see JP-A-58-88334), 1-menthyl 3-hydroxybutyrate (e.g., see JP-A-61-194049), 1-alkoxy-3-(1-menthoxy)propane-2-ol (e.g., see JP-A-2-290827), esters of 3-hydroxymethyl-p-menthane (e.g., see JP-A-5-255186), N-acetylglycinementhane methyl ester (e.g., see JP-A-5-255217), (−)-isopulegol (e.g., see JP-A-6-65023), (2S)-3-(1-menthoxy)propane-1,2-diol (e.g., see JP-A-7-82200), 2-hydroxymethylmenthol (e.g., see JP-A-7-118119) and the like can be mentioned.